Heterocyclic compound and organic light-emitting device including the same

ABSTRACT

A heterocyclic compound represented by Formula 1 and an organic light-emitting device including the same are provided, wherein the substituents in Formula 1 are the same as defined in the detailed descriptions.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2019-0119091, filed on Sep. 26, 2019, in the KoreanIntellectual Property Office, the disclosure of which is incorporatedherein in its entirety by reference.

BACKGROUND 1. Field

One or more embodiments relate to a heterocyclic compound and an organiclight-emitting device including the same.

2. Description of Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, and/or excellent characteristics in termsof brightness, driving voltage, and/or response speed, compared todevices in the related art.

The organic light-emitting device may include a first electrode disposedon a substrate, and a hole transport region, an emission layer, anelectron transport region, and a second electrode, which aresequentially disposed on the first electrode. Holes provided from thefirst electrode may move toward the emission layer through the holetransport region, and electrons provided from the second electrode maymove toward the emission layer through the electron transport region.Carriers, such as holes and electrons, recombine in the emission layerto produce excitons. These excitons transit from an excited state to aground state, thereby generating (e.g., emitting) light.

SUMMARY

An asepect according to one or more embodiments is directed toward anovel heterocyclic compound and an organic light-emitting deviceincluding the same.

Additional aspects will be set forth in part in the description whichfollows and, in part, will be apparent from the description, or may belearned by practice of the presented embodiments of the disclosure.

According to an embodiment of the present disclosure, a heterocycliccompound represented by Formula 1 is provided.

In Formulae 1 to 3,

Y₁ may be O or S,

Cz may be a group represented by Formula 2,

n1 and n2 may each independently be an integer from 0 to 4, and a sum ofn1 and n2 may be 1 or more,

A₁₁, A₁₂, A₂₁, and A₂₂ may each independently be selected from a benzenering, a pyridine ring, a pyrimidine ring, and a pyridazine ring, and atleast one of A₁₁ and A₁₂ may be selected from a pyridine ring, apyrimidine ring, and a pyridazine ring,

L₁, L₂, and L₂₁ to L₂₃ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,

a1, a2, and a21 to a23 may each independently be an integer from 0 to 3,

R₁, R₂, R₂₁, and R₂₂ may each independently be selected from a grouprepresented by Formula 3, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂), wherein atleast one of R₁, R₂, R₂₁, and R₂₂ may be a group represented by Formula3,

R₃, R₄, R₂₃, and R₂₄ may be each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazine group, a hydrazone group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂),

b1, b2, b21, and b22 may each independently be an integer from 1 to 5,

c1, c2, c21, and c22 may each independently be an integer from 1 to 4,

c3, c4, c23, and c24 may each independently be an integer from 0 to 4,

Ar₃₁ to Ar₃₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group,

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆o alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazine group, a hydrazone group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may eachindependently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amino group, an amidinogroup, a hydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, aC₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensedpolycyclic group, a monovalent non-aromatic condensed heteropolycyclicgroup, a biphenyl group, and a terphenyl group, and

* indicates a binding site to a neighboring atom.

According to an embodiment of the present disclosure, an organiclight-emitting device includes: a first electrode; a second electrodefacing the first electrode; and an organic layer between the firstelectrode and the second electrode and including an emission layer;wherein the organic light-emitting device comprises at least oneheterocyclic compound represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, features, and advantages of certainembodiments of the disclosure will be more apparent from the followingdescription taken in conjunction with the accompanying drawings, inwhich:

FIGS. 1-4 are each a schematic view of a structure of an organiclight-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples ofwhich are illustrated in the accompanying drawings, wherein likereference numerals refer to like elements throughout. In this regard,the present embodiments may have different forms and should not beconstrued as being limited to the descriptions set forth herein.Accordingly, the embodiments are merely described below, by referring tothe figures, to explain aspects of the present description. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. Throughout the disclosure, theexpression “at least one of a, b or c” indicates only a, only b, only c,both a and b, both a and c, both b and c, all of a, b, and c, orvariations thereof.

According to an embodiment of the present disclosure, a heterocycliccompound is represented by Formula 1 below:

Y₁ in Formula 1 may be O or S.

Cz in Formula 1 may be a group represented by Formula 2.

In Formula 1, n1 and n2 may each independently be an integer from 0 to4, and the sum of n1 and n2 may be 1 or more.

In Formulae 1 and 2, A₁₁, A₁₂, A₂₁, and A₂₂ may each independently beselected from a benzene ring, a pyridine ring, a pyrimidine ring, and apyridazine ring, and at least one of A₁₁ and A₁₂ may be selected from apyridine ring, a pyrimidine ring, and a pyridazine ring.

In one embodiment, in Formula 1,

A₁₁ may be a benzene ring and A₁₂ may be a pyridine ring,

A₁₁ may be a pyridine ring and A₁₂ may be a benzene ring, or

each of A₁₁ and A₁₂ may be a pyridine ring.

In one embodiment, each of A₂₁ and A₂₂ in Formula 2 may be a benzenering.

In Formulae 1 and 2, L₁, L₂, and L₂₁ to L₂₃ may each independently beselected from a substituted or unsubstituted C₃-C₁₀ cycloalkylene group,a substituted or unsubstituted heterocycloalkylene group, a substitutedor unsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group.

In one embodiment, L₁, L₂, and L₂₁ to L₂₃ in Formulae 1 and 2 may eachindependently be selected from:

a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, abenzofluorenylene group, a dibenzofluorenylene group, a phenalenylenegroup, a phenanthrenylene group, an anthracenylene group, afluoranthenylene group, a triphenylenylene group, a pyrenylene group, achrysenylene group, a naphthacenylene group, a picenylene group, aperylenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a quinolinylene group, an isoquinolinylene group,a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a thiophenylene group, a furanylenegroup, a carbazolylene group, an indolylene group, an isoindolylenegroup, a benzofuranylene group, a benzothiophenylene group, adibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, and adibenzosilolylene group; and

a cyclobutylene group, a cyclopentylene group, a cyclohexylene group, aphenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, abenzofluorenylene group, a dibenzofluorenylene group, a phenalenylenegroup, a phenanthrenylene group, an anthracenylene group, afluoranthenylene group, a triphenylenylene group, a pyrenylene group, achrysenylene group, a naphthacenylene group, a picenylene group, aperylenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a quinolinylene group, an isoquinolinylene group,a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a thiophenylene group, a furanylenegroup, a carbazolylene group, an indolylene group, an isoindolylenegroup, a benzofuranylene group, a benzothiophenylene group, adibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, and adibenzosilolylene group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an am idino group, a hydrazine group, a hydrazone group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group,a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a naphthyridinyl group, a quinoxalinyl group, a quinazolinylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂).

In one or more embodiments, L₁, L₂, and L₂₁ to L₂₃ in Formulae 1 and 2may each independently be selected from:

a phenylene group; and a phenylene group substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazine group, a hydrazonegroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₆-C₂₀ aryl group, a C₁-C₂₀heteroaryl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂).

In one or more embodiments, L₁, L₂, and L₂₁ to L₂₃ in Formulae 1 and 2may each independently be selected from groups represented by Formulae3-1 to 3-38 below:

In Formulae 3-1 to 3-38,

Y₁ may be O, S, C(Z₃)(Z₄), N(Z₅), or Si(Z₆)(Z₇),

Z₁ to Z₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinylgroup, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂),

d2 may be 1 or 2,

d3 may be an integer from 1 to 3,

d4 may be an integer from 1 to 4,

d5 may be an integer from 1 to 5,

d6 may be an integer from 1 to 6,

d8 may be an integer from 1 to 8,

Q₃₁ to Q₃₃ may each independently be selected from hydrogen, deuterium,a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a C₆-C₆₀ aryl group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, abiphenyl group, and a terphenyl group, and

* and *′ each indicate a binding site to a neighboring atom.

In one or more embodiments, L₁, L₂, and L₂₁ to L₂₃ in Formulae 1 and 2may each independently be a group represented by Formula 3-1 or 3-2.

In Formulae 1 and 2, a1, a2, and a21 to a23 may each independently be aninteger from 0 to 3.

When al is 0, *-(L₁)_(a1)-*′ may be a single bond, and when a1 is 2 or3, two or three L₁(s) may be identical to or different from each other.When a2 is 0, *-(L₂)_(a2)-*′ may be a single bond, and when a2 is 2 or3, two or three L₂(s) may be identical to or different from each other.When a21 is 0, *-(L₂₁)_(a21)-*′ may be a single bond, and when a21 is 2or 3, two or three L₂₁(s) may be identical to or different from eachother. When a22 is 0, *-(L₂₂)_(a22)-*′ may be a single bond, and whena22 is 2 or 3, two or three L₂₂(s) may be identical to or different fromeach other. When a23 is 0, *-(L₂₃)_(a23)-′ may be a single bond, andwhen a23 is 2 or 3, two or three L₂₃(s) may be identical to or differentfrom each other.

In one embodiment, a1, a2, and a21 to a23 in Formulae 1 and 2 may eachbe 0 or 1.

In one or more embodiments, a1, a2, a21, and a22 in Formulae 1 and 2 mayeach be 0 or 1, and a23 in Formulae 1 and 2 may be 0.

In Formulae 1 and 2, R₁, R₂, R₂₁, and R₂₂ may each independently beselected from a group represented by Formula 3, hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazine group, a hydrazone group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂),and —P(═O)(Q₁)(Q₂). At least one selected from R₁, R₂, R₂₁, and R₂₂ maybe a group represented by Formula 3.

In one embodiment, R₁, R₂, R₂₁, and R₂₂ in Formulae 1 and 2 may eachindependently be selected from:

a group represented by Formula 3, hydrogen, deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group,and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazine group, a hydrazonegroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group,a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, a silolyl group, an imidazolyl group,a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an oxazolopyridinyl group, athiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenylgroup, an azaspiro-bifluorenyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, a biphenyl group, and a terphenyl group.

In Formulae 1 and 2, R₃, R₄, R₂₃, and R₂₄ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an am idino group, a hydrazine group, ahydrazone group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂).

In one embodiment, R₃, R₄, R₂₃, and R₂₄ in Formulae 1 and 2 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, a C₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, aphenyl group, and a biphenyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group; and

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group, each substituted with at leastone selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an am idino group, a hydrazine group, a hydrazonegroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group,a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group,a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, a silolyl group, an imidazolyl group,a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an oxazolopyridinyl group, athiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenylgroup, an azaspiro-bifluorenyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, a biphenyl group, and a terphenyl group.

In Formulae 1 and 2, b1, b2, b21, and b22 may each independently be aninteger from 1 to 5.

In Formulae 1 and 2, c1, c2, c21, and c22 may each independently be aninteger from 1 to 4, and c3, c4, c23, and c24 may each independently bean integer from 0 to 4.

In one embodiment, Cz in Formula 1 may be a group represented by Formula2A:

In Formula 2A, L₂₁ to L₂₃, a21 to a23, R₂₁ to R₂₄, b21, b22, and c21 toc24 are the same as respectively descirbed above in connection withFormula 2.

In one or more embodiments, Cz in Formula 1 may be a group representedby Formulae 2A-1 to 2A-5:

In Formulae 2A-1 to 2A-5,

R₂₁ may be a group represented by Formula 3,

c23 may be an integer from 0 to 3,

c24 may be an integer from 0 to 4,

and L₂₁, L₂₃, a21, a23, R₂₃, and R₂₄ are the same as respectivelydescribed above in connection with Formula 2.

In Formula 3, Ar₃₁ to Ar₃₃ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group.

In one embodiment, Ar₃₁ to Ar₃₃ may each independently be selected from:

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a spiro-cyclopentane-fluorenyl group,a spiro-cyclohexane-fluorenyl group, a spiro-fluorene-benzofluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, a silolyl group, an imidazolyl group, a pyrazolyl group,a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an indolyl group, an isoindolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzothiazolyl group, a benzosilolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an oxazolopyridinyl group, athiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenylgroup, an azaspiro-bifluorenyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, and anazadibenzosilolyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenylgroup, an indenyl group, a naphthyl group, an azulenyl group, aheptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a spiro-cyclopentane-fluorenyl group,a spiro-cyclohexane-fluorenyl group, a spiro-fluorene-benzofluorenylgroup, a benzofluorenyl group, a dibenzofluorenyl group, a pyrenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, anaphthacenyl group, a picenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pyrrolyl group, a thiophenyl group, afuranyl group, a silolyl group, an imidazolyl group, a pyrazolyl group,a thiazolyl group, an isothiazolyl group, an oxazolyl group, anisoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a pyridazinyl group, an indolyl group, an isoindolyl group, anindazolyl group, a purinyl group, a quinolinyl group, an isoquinolinylgroup, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzothiazolyl group, a benzosilolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an oxazolopyridinyl group, athiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenylgroup, an azaspiro-bifluorenyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, and anazadibenzosilolyl group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazine group, a hydrazone group, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₃-C₁₀ cycloalkenyl group, a C₆-C₂₀ aryl group, a C₁-C₂₀ heteroarylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂).

In one or more embodiments, Ar₃₁ to Ar₃₃ may each independently beselected from:

a phenyl group; and a phenyl group substituted with at least oneselected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazine group, a hydrazonegroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₆-C₂₀ aryl group, a C₁-C₂₀heteroaryl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂).

In one or more embodiments, Ar₃₁ to Ar₃₃ may each independently beselected from groups represented by Formulae 5-1 to 5-81 below:

In Formulae 5-1 to 5-81,

Y₃₁ may be selected from O, S, N(Z₃₃), C(Z₃₄)(Z₃₅), and Si(Z₃₆)(Z₃₇),

Z₃₁ to Z₃₇ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀ alkylgroup, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, acycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenylgroup, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinylgroup, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂),

e2 may be 1 or 2,

e3 may be an integer from 1 to 3,

e4 may be an integer from 1 to 4,

e5 may be an integer from 1 to 5,

e6 may be an integer from 1 to 6,

e7 may be an integer from 1 to 7,

e9 may be an integer from 1 to 9,

Q₃₁ to Q₃₃ may each independently be selected from hydrogen, deuterium,a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryl group, aC₁-C₂₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, a monovalent non-aromatic condensed heteropolycyclic group, abiphenyl group, and a terphenyl group, and

* indicates a binding site to a neighboring atom.

In one embodiment, in Formula 1, i) n1 may be 1, n2 may be 0, and atleast one of R₁ and R₂ may be a group represented by Formula 3, or ii)n1 may be 1, n2 may be 0, and at least one of R₂₁ and R₂₂ may be a grouprepresented by Formula 3.

In one or more embodiments, in Formula 1, i) n1 may be 1, n2 may be 0,and R₂ may be a group represented by Formula 3, or ii) n1 may be 1, n2may be 0, and R₂₁ or R₂₂ may be a group represented by Formula 3.

In one embodiment, the heterocyclic compound may be represented byFormula 1A:

In Formula 1A,

X₁ may be C or N, X₂ may be C or N, X₄ may be C or N, X₅ may be C or N,X₆ may be C or N, X₇ may be C or N, and X₈ may be C or N,

at least one of X₁, X₂, and X₄ to X₈ may be N,

c1 may be an integer from 1 to 3,

c2 may be an integer from 1 to 4,

c3 may be an integer from 0 to 2,

c4 may be an integer from 0 to 3,

Y₁, Cz, L₁, L₂, a1, a2, R₁ to R₄, and b1 to b4 may each be understood byreferring to the respective descriptions thereof presented in connectionwith Formula 1.

That is, Y₁, Cz, L₁, L₂, a1, a2, R₁ to R₄, and b1 to b4 may each be thesame as respectively defined in connection with Formula 1.

In one embodiment, in Formula 1A,

one of X₁, X₂, and X₄ to X₈ may be N, and the others (i.e., theremaining ones of X₁, X₂, and X₄ to X₈) may each be C,

X₁ and X₈ may each be N, and X₂ and X₄ to X₇ may each be C,

X₂ and X₅ may each be N, and X₁, X₄, and X₆ to X₈ may each be C,

X₂ and X₈ may each be N, and X₁ and X₄ to X₇ may each be C,

X₄ and X₅ may each be N, and X₁, X₂, and X₆ to X₈ may each be C,

X₄ and X₇ may each be N, and X₁, X₂, X₅, X₆, and X₈ may each be C, or

X₄ and X₈ may each be N, and X₁, X₂, and X₅ to X₇ may each be C.

In one embodiment, the heterocyclic compound may be represented by oneof Formulae 1A-1 to 1A-8:

In Formulae 1A-1 to 1A-8,

X₁ may be C or N, X₂ may be C or N, X₄ may be C or N, X₅ may be C or N,X₆ may be C or N, X₇ may be C or N, and X₈ may be C or N,

at least one of X₁, X₂, and X₄ to X₈ may be N,

in Formulae 1A-1 to 1A-4, R₂₁ may be a group represented by Formula 3,c3 may be an integer from 0 to 3, c4 may be an integer from 0 to 4, c23may be an integer from 0 to 3, and c24 may be an integer from 0 to 4,

in Formulae 1A-5 to 1A-8 , R₂ may be a group represented by Formula 3,c3 and c4 may each independently be an integer from 0 to 3, and c23 andc24 may each independently be an integer from 0 to 4, and

Y₁, L₂, L₂₁, a2, a21, R₃, R₄, R_(23,) and R₂₄ may each be understood byreferring to the respective descriptions thereof presented in connectionwith Formulae 1 and 2. That is, Y₁, L₂, L₂₁, a2, a21, R₃, R₄, R₂₃, andR₂₄ may each be the same as respectively defined in connection withFormulae 1 and 2.

In one embodiment, in Formulae 1A-1 to 1A-8,

one of X₁, X₂, and X₄ to X₈ may be N, and the others (i.e., theremaining ones of X₁, X₂, and X₄ to X₈) may each be C,

X₁ and X₈ may each be N, and X₂ and X₄ to X₇ may each be C,

X₂ and X₅ may each be N, and X₁, X₄, and X₆ to X₈ may each be C,

X₂ and X₈ may be each N, and X₁ and X₄ to X₇ may each be C,

X₄ and X₅ may each be N, and X₁, X₂, and X₆ to X₈ may each be C,

X₄ and X₇ may each be N, and X₁, X₂, X₅, X_(6,) and X₈ may each be C, or

X₄ and X₈ may each be N, and X₁, X₂, and X₅ to X₇ may each be C.

In one embodiment, the heterocyclic compound may be selected fromCompounds 1 to 35, but embodiments of the present disclosure are notlimited thereto:

The heterocyclic compound represented by Formula 1 may be a bipolarcompound including both an azadibenzofuran or azadibenzothiophenemoiety, having suitable (e.g., excellent) electron withdrawing group(EWG) property, and a carbazole-based moiety, having suitable (e.g.,excellent) electron donating group (EDG) property.

When an emission layer of an organic light-emitting device includes anelectron transport host material only, or includes a hole transport hostmaterial only, depending on characteristics of the host material of theemission layer, the host material may deteriorate due to a weakstability against an opposite charge. In contrast, a heterocycliccompound according to an embodiment may have a bipolar characteristicand may be used as a host material, and thus deterioration of the hostmaterial may be reduced or prevented. Therefore, the organiclight-emitting device including the heterocyclic compound may haveimproved durability and lifespan.

In the emission layer including a unipolar host material (i.e., a hostmaterial with only electron withdrawing property or only electrondonating property), excitons are formed mainly at an emission layerinterface on a side of the first electrode or an emission layerinterface on a side of the second electrode according to a chargetransport capability of the emission layer host material. Accordingly,the excitons are easily diffused or moved to an organic layer adjacentto the emission layer, for example, a hole transport region or aelectron transport region, thereby deteriorating the lifespan of theorganic light-emitting device due to deterioration of a hole transportmaterial or an electron transport material. Because the heterocycliccompound according to embodiments of the present disclosure may bebipolar, the heterocyclic compound may have suitable (e.g., excellent)charge injection and charge transport characteristics, and thus theheterocyclic compound may substantially confine the excitons in theemission layer and may prevent or substantially prevent the excitonsfrom diffusing and moving to the hole transport region or electrontransport region. Therefore, the organic light-emitting device includingthe heterocyclic compound may have improved lifespan.

Because the heterocyclic compound includes at least one silyl grouprepresented by Formula 3 and replaces a hydrogen at the end of thebenzene ring with Si of the silyl group, the stability may be increasedby controlling dropping of a hydrogen atom or a radical reaction.Furthermore, because an electronegativity of Si is lower than anelectronegativity of C, a C—Si bond forms a bond in which a sp³ orbitaland a sp² orbital are mixed, thereby forming a stronger bond than a C—Cbond formed by a sp³ orbital. Furthermore, the silyl group representedby Formula 3 increases a steric effect and thus the heterocycliccompound may have a higher T1.

Furthermore, at least one of A₁₁ and A₁₂ is selected from a pyridinering, a pyrimidine ring, and a pyridazine ring such that the electrondensity of peripheral carbon atoms may decrease according to theelectron withdrawing characteristic of a 7 electron-depleted nitrogenatom. Accordingly, bonds around the nitrogen atom may have a strongerionic bond characteristic, and thus may form a stronger bond. Therefore,a bond dissociation energy of the heterocyclic compound may becomegreater, and thus may have the improved compound stability even in acharged state. Furthermore, because the heterocyclic compound may havethe greater electron transport capability, the organic light-emittingdevice including the heterocyclic compound may effectively achievecharge balance. Therefore, the organic light-emitting device includingthe heterocyclic compound may have improved lifespan.

Therefore, an electronic device, such as an organic light-emittingdevice, including the heterocyclic compound may have low drivingvoltage, high efficiency, and/or long lifespan.

A synthesis method for the heterocyclic compound represented by Formula1 would be apparent to those of ordinary skill in the art by referringto the following examples.

The heterocyclic compound represented by Formula 1 may be utilizedbetween a pair of electrodes of an organic light-emitting device. Forexample, the heterocyclic compound may be included in at least one layerselected from a hole transport region, an electron transport region, andan emission layer. In one or more embodiments, the heterocyclic compoundof Formula 1 may be utilized as a material for a capping layer locatedoutside a pair of electrodes of an organic light-emitting device.

Accordingly, another embodiment of the present disclosure provides anorganic light-emitting device including: a first electrode; a secondelectrode facing the first electrode; an organic layer disposed betweenthe first electrode and the second electrode and including an emissionlayer; and at least one heterocyclic compound represented by Formula 1.

In one embodiment, the organic layer of the organic light-emittingdevice may include at least one heterocyclic compound represented byFormula 1.

The expression “(an organic layer) includes at least one heterocycliccompound” as used herein may include a case in which “(an organic layer)includes identical heterocyclic compounds represented by Formula 1” anda case in which “(an organic layer) includes two or more differentheterocyclic compounds represented by Formula 1”.

In one embodiment, the emission layer of the organic light-emittingdevice may include at least one heterocyclic compound represented byFormula 1. The heterocyclic compound included in the emission layer mayserve as a host, and the emission layer may further include at least oneselected from a phosphorescent dopant and a fluorescent dopant.

In one embodiment, the emission layer of the organic light-emittingdevice may include at least one heterocyclic compound represented byFormula 1, and the heterocyclic compound included in the emission layermay serve as a host, and the emission layer may further include at leastone of an electron transport host and a hole transport host.

In one or more embodiments, the emission layer of the organiclight-emitting device may include at least one heterocyclic compoundrepresented by Formula 1, and the heterocyclic compound included in theemission layer may serve as a host, and the emission layer may furtherinclude an electron transport host including at least one πelectron-depleted nitrogen-containing ring.

The π electron-depleted nitrogen-containing ring included in theelectron transport host may be selected from a triazine, a pyridine, apyrimidine, a phenanthroline, and a triazole.

In one embodiment, the organic layer may further include at least onelayer selected from an electron blocking layer disposed between thefirst electrode and the emission layer and a hole blocking layerdisposed between the emission layer and the second electrode. Theelectron blocking layer or the hole blocking layer may directly contactthe emission layer.

In one embodiment, the electron blocking layer or the hole blockinglayer may include the heterocyclic compound represented by Formula 1.

In one or more embodiments, the organic layer may include an electronblocking layer, and the emission layer and the electron blocking layermay each include the heterocyclic compound represented by Formula 1,wherein the heterocyclic compound included in the emission layer and theheterocyclic compound included in the electron blocking layer may beidentical to or different from each other.

In one or more embodiments, the organic layer may include a holeblocking layer, and the emission layer and the hole blocking layer mayeach include the heterocyclic compound represented by Formula 1, whereinthe heterocyclic compound included in the emission layer and theheterocyclic compound included in the hole blocking layer may beidentical to or different from each other.

In one or more embodiments, the emission layer may include theheterocyclic compound represented by Formula 1 and may further includean electron transport host, and the organic layer may further include ahole blocking layer including a electron transporting compound, whereinthe electron transporting compound included in the hole blocking layermay be identical to the heterocyclic compound represented by Formula 1included in the emission layer.

In one embodiment, the first electrode may be an anode, the secondelectrode may be a cathode, and the organic layer may further include ahole transport region between the first electrode and the emission layerand an electron transport region between the emission layer and thesecond electrode, wherein the hole transport region may include a holeinjection layer, a hole transport layer, an emission auxiliary layer,and/or an electron blocking layer, and the electron transport region mayinclude a buffer layer, a hole blocking layer, an electron transportlayer, and/or an electron injection layer.

In one embodiment, the hole transport region may include a p-dopanthaving a lowest unoccupied molecular orbital (LUMO) level of −3.5 eV orless.

The term “an organic layer” as used herein refers to a single layerand/or a plurality of layers disposed between the first electrode andthe second electrode of an organic light-emitting device. A materialincluded in the “organic layer” is not limited to an organic material.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of an organic light-emittingdevice 10 according to an embodiment. The organic light-emitting device10 includes a first electrode 110, an organic layer 150, and a secondelectrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with FIG. 1.

First Electrode 110

In FIG. 1, a substrate may be additionally disposed under the firstelectrode 110 or above the second electrode 190. The substrate may be aglass substrate or a plastic substrate, each having suitable (e.g.,excellent) mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and/or water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for forming the firstelectrode 110 may be selected from materials with a high work functionto facilitate hole injection.

The first electrode 110 may be a reflective electrode, a semi-reflectiveelectrode, or a transmissive electrode. When the first electrode 110 isa transmissive electrode, a material for forming a first electrode maybe selected from indium tin oxide (ITO), indium zinc oxide (IZO), tinoxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, butembodiments of the present disclosure are not limited thereto. In one ormore embodiments, when the first electrode 110 is a semi-transmissiveelectrode or a reflectable electrode, a material for forming the firstelectrode may be selected from magnesium (Mg), silver (Ag), aluminum(Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In),magnesium-silver (Mg—Ag), and any combinations thereof, but embodimentsof the present disclosure are not limited thereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

Organic Layer 150

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer and an electrontransport region between the emission layer and the second electrode190.

Hole Transport Region in Organic Layer 150

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in the stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB(NPD), β-NPB, TPD, spiro-TPD, spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *-O-*′, *-N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one embodiment, in Formula 202, R₂₀₁ and R₂₀₂ may optionally belinked to each other via a single bond, a dimethyl-methylene group, or adiphenyl-methylene group, and R₂₀₃ and R₂₀₄ may optionally be linked toeach other via a single bond, a dimethyl-methylene group, or adiphenyl-methylene group.

In one or more embodiments, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an am idino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂);

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above in association with L₂₀₁ toL₂₀₅.

In one or more embodiments, R₂₀₁ to R₂₀₃ in Formula 201 may eachindependently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinegroup, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked to each other via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may belinked to each other via a single bond.

In one or more embodiments, R₂₀₁ to R₂₀₄ in Formula 202 may eachindependently be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201-1 below:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201-2 below, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201-2(1) below, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A below:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A(1) below, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the compound represented by Formula 201 maybe represented by Formula 201A-1 below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202-1 below:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202-1(1) below:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A below:

In one or more embodiments, the compound represented by Formula 202 maybe represented by Formula 202A-1 below:

In Formulae 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1,202-1(1), 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂ to R₂₀₄ may each be understoodby referring to corresponding descriptions presented herein inassociation with Formulae 201 and 202,

L₂₀₅ may be selected from a phenylene group and a fluorenylene group,

X₂₁₁ may be selected from O, S, and N(R₂₁₁),

X₂₁₂ may be selected from O, S, and N(R₂₁₂),

R₂₁₁ and R₂₁₂ may each be understood by referring to correspondingdescriptions provided in connection with R₂₀₃ in association withFormulae 201 and 202, and

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT48 below, but embodiments of the presentdisclosure are not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one selected from a holeinjection layer and a hole transport layer, the thickness of the holeinjection layer may be in a range of about 100 Å to about 9,000 Å, andfor example, about 100 Å to about 1,000 Å, and the thickness of the holetransport layer may be in a range of about 50 Å to about 2,000 Å, andfor example, about 100 Å to about 1500 Å. When the thicknesses of thehole transport region, the hole injection layer, and the hole transportlayer are within these ranges, satisfactory hole transportingcharacteristics may be obtained without a substantial increase indriving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

p-Dopant

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a LUMO energy level of −3.5 eVor less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

In one embodiment, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and/or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide and/or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

F6-TNAP, Compound 201, and Compound 202; and

a compound represented by Formula 221 below,

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br, and a C₁-C₂₀ alkyl group substituted with —I.

Emission Layer in Organic Layer 150

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

In the emission layer, an amount of the dopant may be in a range ofabout 0.01 parts by weight to about 15 parts by weight based on 100parts by weight of the host, but embodiments of the present disclosureare not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within these ranges, suitable (e.g.,excellent) light-emission characteristics may be obtained without asubstantial increase in driving voltage.

Host in Emission Layer

The host may include a compound represented by Formula 1.

The host may include the heterocyclic compound represented by Formula 1,and may further include at least one selected from an electron transporthost and a hole transport host.

In one or more embodiments, the host may further include a compoundrepresented by Formula 301 below:

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21)   Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an am idino group, a hydrazine group, ahydrazone group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

When xb11 in Formula 301 is 2 or more, two or more Ar₃₀₁(s) may belinked to each other via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2 below:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene, anaphthalene, a phenanthrene, a fluoranthene, a triphenylene, a pyrene, achrysene, a pyridine, a pyrimidine, an indene, a fluorene, aspiro-bifluorene, a benzofluorene, a dibenzofluorene, an indole, acarbazole, benzocarbazole, dibenzocarbazole, a furan, a benzofuran, adibenzofuran, a naphthofuran, a benzonaphthofuran, dinaphthofuran, athiophene, a benzothiophene, a dibenzothiophene, a naphthothiophene, abenzonaphthothiophene, and a dinaphthothiophene,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₃ may each be understood by referring tocorresponding descriptions presented herein in connection with Forula301,

L₃₀₂ to L₃₀₄ may each be understood by referring to the descriptionprovided herein in connection with L₃₀₁,

xb2 to xb4 may each be understood by referring to the descriptionprovided herein in connection with xb1, and

R₃₀₂ to R₃₀₄ may be understood by referring to the description providedherein in connection with R₃₀₁.

For example, L₃₀₁ to L₃₀₄ in Formulae 301, 301-1, and 301-2 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above in connection with Formula301.

In one embodiment, R₃₀₁ to R₃₀₄ in Formulae 301, 301-1, and 301-2 mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ and Q₃₃ are the same as described above in connection with Formula301.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyI)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

Phosphorescent Dopant Included in Emission Layer in Organic Layer 150

The phosphorescent dopant may include an organometallic complexrepresented by Formula 401 below:

In Formulae 401 and 402,

M may be selected from iridium (Ir), platinum (Pt), palladium (Pd),osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu),terbium (Tb), rhodium (Rh), and thulium (Tm),

L₄₀₁ may be selected from ligands represented by Formula 402, and xc1may be 1, 2, or 3, wherein, when xc1 is two or more, two or more L₄₀₁(s)may be identical to or different from each other,

L₄₀₂ may be an organic ligand, and xc2 may be an integer from 0 to 4,wherein, when xc2 is two or more, two or more L₄₀₂(s) may be identicalto or different from each other,

X₄₀₁ to X₄₀₄ may each independently be nitrogen or carbon,

X₄₀₁ and X₄₀₃ may be linked via a single bond or a double bond, and X₄₀₂and X₄₀₄ may be linked via a single bond or a double bond,

A₄₀₁ and A₄₀₂ may each independently be selected from a C₅-C₆₀carbocyclic group or a C₁-C₆₀ heterocyclic group,

X₄₀₅ may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′,*—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C(Q₄₁₁)=*′,wherein Q₄₁₁ and Q₄₁₂ may each independently be hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenylgroup, a terphenyl group, or a naphthyl group,

X₄₀₆ may be a single bond, O, or S,

R₄₀₁ and R₄₀₂ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, asubstituted or unsubstituted C₁-C₂₀ alkyl group, a substituted orunsubstituted C₁-C₂₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂),—B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂),wherein Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀ alkoxy group, a C₆-C₂₀ aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 10, and

* and *′ in Formula 402 each indicate a binding site to M in Formula401.

In one embodiment, A₄₀₁ and A₄₀₂ in Formula 402 may each independentlybe selected from a benzene group, a naphthalene group, a fluorene group,a spiro-bifluorene group, an indene group, a pyrrole group, a thiophenegroup, a furan group, an imidazole group, a pyrazole group, a thiazolegroup, an isothiazole group, an oxazole group, an isoxazole group, apyridine group, a pyrazine group, a pyrimidine group, a pyridazinegroup, a quinoline group, an isoquinoline group, a benzoquinoline group,a quinoxaline group, a quinazoline group, a carbazole group, abenzimidazole group, a benzofuran group, a benzothiophene group, anisobenzothiophene group, a benzoxazole group, an isobenzoxazole group, atriazole group, a tetrazole group, an oxadiazole group, a triazinegroup, a dibenzofuran group, and a dibenzothiophene group.

In one or more embodiments, in Formula 402, i) X₄₀₁ may be nitrogen, andX₄₀₂ may be carbon, or ii) each of X₄₀₁ and X₄₀₂ may be nitrogen.

In one or more embodiments, R₄₀₁ and R₄₀₂ in Formula 501 may eachindependently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₂₀ alkyl group, and a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazine group, ahydrazone group, a phenyl group, a naphthyl group, a cyclopentyl group,a cyclohexyl group, an adamantanyl group, a norbornanyl group, and anorbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group a phenyl group, a biphenyl group,a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinylgroup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinegroup, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, an adamantanyl group, anorbornanyl group, a norbornenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a naphthyl group, a fluorenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁),—S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁ to Q₄₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, and anaphthyl group, but embodiments of the present disclosure are notlimited thereto.

In one or more embodiments, when xc1 in Formula 401 is 2 or more, twoA₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, whichis a linking group; or two A₄₀₂(s) in two or more L₄₀₁(s) may optionallybe linked via X₄₀₈, which is a linking group (see Compounds PD1 to PD4and PD7). X₄₀₇ and X₄₀₈ may each independently be a single bond, *—O—*′,*—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)—*′, *—C(Q₄₁₃)(Q₄₁₄)—*′, or*—C(Q₄₁₃)=C(Q₄₁₄)-*′ (wherein Q₄₁₃ and Q₄₁₄ may each independently behydrogen, deuterium, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, or a naphthyl group),but embodiments of the present disclsoure are not limited thereto.

L₄₀₂ in Formula 401 may be a monovalent, divalent, or trivalent organicligand. For example, L₄₀₂ may be selected from halogen, diketone (forexample, acetylacetonate), carboxylic acid (for example, picolinate),—C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, orphosphite), but embodiments of the present disclosure are not limitedthereto.

In one or more embodiments, the phosphorescent dopant may be selectedfrom, for example, Compounds PD1 to PD25, but embodiments of the presentdisclosure are not limited thereto:

Fluorescent Dopant in Emission Layer

The fluorescent dopant may include an arylamine compound and/or astyrylamine compound.

The fluorescent dopant may include a compound represented by Formula 501below:

In Formula 501,

Ar₅₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

L₅₀₁ to L₅₀₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁ and R₅₀₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,and

xd4 may be an integer from 1 to 6.

In one embodiment, Ar₅₀₁ in Formula 501 may be selected from:

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup; and

a naphthalene group, a heptalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, and an indenophenanthrenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group,a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, L₅₀₁ to L₅₀₃ in Formula 501 may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, and a pyridinylene group, each substituted withat least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an am idino group, a hydrazinegroup, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group.

In one or more embodiments, R₅₀₁ and R₅₀₂ in Formula 501 may eachindependently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, and a pyridinyl group, each substituted with atleast one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazine group, ahydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenylgroup, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xd4 in Formula 501 may be 2, but embodimentsof the present disclosure are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1to FD24 below:

In one or more embodiments, the fluorescent dopant may be selected fromthe following compounds, but embodiments of the present disclosure arenot limited thereto:

Electron Transport Region in Organic Layer 150

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from the emission layer. However, embodiments ofthe present disclosure are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, and/or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one π electron-depleted nitrogen-containingring.

The term “π electron-depleted nitrogen-containing ring” refers to aC₁-C₆₀ heterocyclic group having at least one *—N═*′ moiety as aring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 5-membered to 7-membered heteromonocyclic group having at least one*—N═*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N═*′ moiety are condensed with each other, or iii) aheteropolycyclic group in which at least one of 5-membered to 7-memberedheteromonocyclic groups, each having at least one *—N═*′ moiety, iscondensed with at least one C₅-C₆₀ carbocyclic group.

Examples of the π electron-depleted nitrogen-containing ring include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, anindazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, aphthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline,a phenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, animidazopyridine, an imidazopyrimidine, and an azacarbazole, butembodiments of the present disclsoure are not limited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601 below:

[Ar₆₀₁]_(xe11)-[(L₆₀₁)_(xe1)-R₆₀₁]_(xe21)   Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁ (S) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, Ar₆₀₁ in Formula 601 may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, a phenazine group, abenzimidazole group, an isobenzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazole group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinegroup, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anda naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more Ar₆₀₁(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may berepresented by Formula 601-1 below:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), X₆₁₆ may be N orC(R₆₁₆), and at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each be understood by referring to correspondingdescriptions provided in connection with L₆₀₁,

xe611 to xe613 may each be understood by referring to correspondingdescriptions provided in connection with xe1,

R₆₁₁ to R₆₁₃ may each be understood by referring to correspondingdescriptions provided in connection with R₆₀₁,

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an am idino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, L₆₀₁ and L₆₁₁ to L₆₁₃ in Formulae 601 and 601-1 mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an am idino group, ahydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, R₆₀₁ and R₆₁₁ to R₆₁₃ in Formula 601 and601-1 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described above in connection with Formula601.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36 below, but embodiments of the presentdisclosure are not limited thereto:

In one or more embodiments, the electron transport region may include atleast one compound selected from2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAIq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ), and NTAZ:

Thicknesses of the buffer layer, the hole blocking layer, and theelectron control layer may each independently be in a range of about 20Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When thethicknesses of the buffer layer, the hole blocking layer, and theelectron control layer are within these ranges, the buffer layer, thehole blocking layer, and/or the electron control layer may have suitable(e.g., excellent) hole blocking characteristics or electron controlcharacteristics without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangesdescribed above, the electron transport layer may have satisfactoryelectron transport characteristics without a substantial increase indriving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected fromhydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxyacridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) or ET-D2:

The electron transport region may include an electron injection layerthat facilitates electron injection from the second electrode 190. Theelectron injection layer may be in direct contact with the secondelectrode 190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combination thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, and/or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, and/or K₂O, and alkali metal halides, such as LiF, NaF,CsF, KF, LiI, NaI, CsI, and/or KI. In one embodiment, the alkali metalcompound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, BaxSr_(1-x)O (0<x<1), and/orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, Sc₂O₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and/or rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, and/or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (e.g., consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth-metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combination thereof, as described above. In one ormore embodiments, the electron injection layer may further include anorganic material. When the electron injection layer further includes theorganic material, the alkali metal, the alkaline earth metal, the rareearth metal, the alkali metal compound, the alkaline earth-metalcompound, the rare earth metal compound, the alkali metal complex, thealkaline earth-metal complex, the rare earth metal complex, or thecombination thereof may be homogeneously or non-homogeneously dispersedin a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the ranges describedabove, the electron injection layer may have satisfactory electroninjection characteristics without a substantial increase in drivingvoltage.

Second Electrode 190

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from a metal, an alloy, anelectrically conductive compound, and combinations thereof, which have arelatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second 190 may have a single-layered structure, or a multi-layeredstructure including two or more layers.

Description of FIGS. 2 to 4

An organic light-emitting device 20 of FIG. 2 includes a first cappinglayer 210, the first electrode 110, the organic layer 150, and thesecond electrode 190, which are sequentially stacked in this statedorder; an organic light-emitting device 30 of FIG. 3 includes the firstelectrode 110, the organic layer 150, the second electrode 190, and asecond capping layer 220, which are sequentially stacked in this statedorder; and an organic light-emitting device 40 of FIG. 4 includes thefirst capping layer 210, the first electrode 110, the organic layer 150,the second electrode 190, and the second capping layer 220, which aresequentially stacked in this stated order.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150,and the second electrode 190 may be understood by referring to thedescription presented in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices20 and 40, light generated in an emission layer may pass through thefirst electrode 110 and the first capping layer 210 toward the outside,wherein the first electrode 110 may be a semi-transmissive electrode ora transmissive electrode.

The first capping layer 210 and the second capping layer 220 mayincrease external luminescent efficiency according to the principle ofconstructive interference.

The first capping layer 210 and the second capping layer 220 may eachindependently be an organic capping layer including an organic material,an inorganic capping layer including an inorganic material, or acomposite capping layer including an organic material and an inorganicmaterial.

At least one selected from the first capping layer 210 and the secondcapping layer 220 may each independently include a carbocyclic compound,a heterocyclic compound, an amine-based compound, a porphyrinederivative, a phthalocyanine derivative, a naphthalocyanine derivative,an alkali metal complexe, and/or an alkaline earth-based complexe. Thecarbocyclic compound, the heterocyclic compound, and/or the amine-basedcompound may be optionally substituted with a substituent containing atleast one element selected from O, N, S, Se, Si, F, Cl, Br, and I. Inone embodiment, at least one selected from the first capping layer 210and the second capping layer 220 may each independently include anamine-based compound.

In one embodiment, at least one selected from the first capping layer210 and the second capping layer 220 may each independently include thecompound represented by Formula 201 or the compound represented byFormula 202.

In one or more embodiments, at least one selected from the first cappinglayer 210 and the second capping layer 220 may each independentlyinclude a compound selected from Compounds HT28 to HT33 and CompoundsCP1 to CP5, but embodiments of the present disclosure are not limitedthereto.

Hereinbefore, the organic light-emitting device according to one ormoreembodiments has been described in connection with FIGS. 1 to 4, butembodiments of the present disclosure are not limited thereto.

Layers constituting the hole transport region, the emission layer, andlayers constituting the electron transport region may each be formed ina certain region by utilizing one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, the emission layer,and/or layers constituting the electron transport region are formed byvacuum deposition, the deposition may be performed at a depositiontemperature of about 100° C. to about 500° C., a vacuum degree of about10⁻⁸ torr to about 10⁻³ torr, and a deposition speed of about 0.01 Å/secto about 100 Å/sec by taking into account a material to be included in alayer to be formed, and the structure of a layer to be formed.

When the layers constituting the hole transport region, the emissionlayer, and/or the layers constituting the electron transport region areformed by spin coating, the spin coating may be performed at a coatingspeed of about 2,000 rpm to about 5,000 rpm and at a heat treatmenttemperature of about 80° C. to 200° C. by taking into account a materialto be included in a layer to be formed, and the structure of a layer tobe formed.

General Definition of Substituents

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and non-limiting examples thereof include a methyl group,an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an isoamyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₆₀ alkyl group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon double bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and non-limiting examplesthereof include an ethenyl group, a propenyl group, and a butenyl group.The term “C₂-C₆₀ alkenylene group” as used herein refers to a divalentgroup having the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and non-limiting examplesthereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having thesame structure as the C₂-C₆₀ alkynyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and non-limiting examples thereof include a methoxy group, an ethoxygroup, and an isopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andnon-limiting examples thereof include a cyclopropyl group, a cyclobutylgroup, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.The term “C₃-C₁₀ cycloalkylene group” as used herein refers to adivalent group having the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andnon-limiting examples thereof include a 1,2,3,4-oxatriazolidinyl group,a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and non-limiting examples thereof include a cyclopentenyl group, acyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group havingthe same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one double bond in its ring. Non-limiting examples of theC₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolylgroup, a 2,3-dihydrofuranyl group, and a2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having the samestructure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, andthe term “C₆-C₆₀ arylene group” as used herein refers to a divalentgroup having a carbocyclic aromatic system having 6 to 60 carbon atoms.Non-limiting examples of the C₆-C₆₀ aryl group include a phenyl group, anaphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenylgroup, and a chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused toeach other.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a carbocyclic aromaticsystem that has at least one heteroatom selected from N, O, Si, P, and Sas a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other.

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and the term “C₆-C₆₀ arylthio group” asused herein refers to —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other, only carbonatoms as the ring-forming atoms, and no aromaticity in its entiremolecular structure. A non-limiting example of the monovalentnon-aromatic condensed polycyclic group is a fluorenyl group. The term“divalent non-aromatic condensed polycyclic group” as used herein refersto a divalent group having the same structure as the monovalentnon-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure. A non-limiting example of the monovalentnon-aromatic condensed heteropolycyclic group is a carbazolyl group. Theterm “divalent non-aromatic condensed heteropolycyclic group” as usedherein refers to a divalent group having the same structure as themonovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 5 to 60 carbon atoms in which thering-forming atoms include only carbon atoms. The term “C₅-C₆₀carbocyclic group” as used herein refers to an aromatic carbocyclicgroup or a non-aromatic carbocyclic group. The C₅-C₆₀ carbocyclic groupmay be a ring (such as benzene), a monovalent group (such as a phenylgroup), or a divalent group (such as a phenylene group). In one or moreembodiments, depending on the number of substituents connected to theC₅-C₆₀ carbocyclic group, the C₅-C₆₀ carbocyclic group may be atrivalent group or a quadrivalent group.

The term “C₁-C₆₀ heterocyclic group” as used herein refers to a grouphaving the same structure as the C₅-C₆₀ carbocyclic group, except thatas a ring-forming atom, at least one heteroatom selected from N, O, Si,P, and S is used in addition to carbon atom(s) (the number of carbonatoms may be in a range of 1 to 60).

In the present specification, at least one substituent of thesubstituted C₅-C₆₀ carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazine group, a hydrazone group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazine group, ahydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” asused herein refers to a methyl group, the term “Et” as used hereinrefers to an ethyl group, the term “ter-Bu” or “Bu^(t)” as used hereinrefers to a tert-butyl group, and the term “OMe” as used herein refersto a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl groupsubstituted with a phenyl group.” In other words, the “biphenyl group”is a substituted phenyl group having a C₆-C₆₀ aryl group as asubstituent.

The term “terphenyl group” as used herein refers to “a phenyl groupsubstituted with a biphenyl group.” In other words, the “terphenylgroup” is a phenyl group having, as a substituent, a C₆-C₆₀ aryl groupsubstituted with a C₆-C₆₀ aryl group.

* and *′ as used herein, unless defined otherwise, each refer to abinding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The wording “Bwas utilized instead of A” used in describing Synthesis Examples refersto that an identical molar equivalent of B was utilized in place of A.

EXAMPLES Synthesis Example Synthesis Example 1: Synthesis of Compound 9

Synthesis of Intermediate 9-1

After 5.9 g of (2-Methoxypyridin-3-yl) boronic acid, 9.8 g of6-chloro-4-iodopyridin-3-amine, 16 g of potassium carbonate, 250 mL oftoluene, 13 mL of distilled water, and 1.3 g ofTetrakis(triphenylphosphine)palladium(0) were mixed and reacted, 5 ml ofTHF, 10 ml of glacial acetic acid, and 11.3 g of tert-butyl nitrite wereadded thereto for further reaction. The obtained compound was dilutedwith water, and then separated and purified by silica gel columnchromatography to obtain 3.2 g of Intermediate 9-1.

Synthesis of Compound 9

3.2 g of Intermediate 9-1, 2.8 g of carbazole, 3.1 g of[3-(triphenylsilyl)phenyl]boronic acid, 0.16 g oftetrakis(triphenylphophine) palladium, 8.2 g of sodium tert butoxide,and 480 mg of 2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl weredissolved in 170 ml of xylene and distilled for two days under N₂atmosphere. The reaction compound was dried with magnesium sulfate, andthe residue obtained by evaporating a solvent was separated and purifiedby silica gel column chromatography to obtain 1.9 g (78% yield) ofCompound 9. Compound 9 was identified by LC-MS and ¹H -NMR.

Synthesis Example 2: Synthesis of Compound 13

Synthesis of Intermediate 13-1

After 9.5 g of 2-methoxyphenylboronic acid, 5.6 g of5-chloro-3-iodopyridin-2-amine, 15.4 g of potassium carbonate, 230 ml oftoluene, 120 ml of distilled water, and 1.3 g oftetrakis(triphenylphophine) palladium were mixed and reacted, 30 ml ofTHF, 50 ml of acetic acid, and 7 ml of tert-butyl nitrite weresubsequently added thereto and reacted to obtain 3.2 g of Intermediate13-1 (yield of 65%, Mass 204).

Synthesis of Compound 13

3.2 g of Intermediate 13-1, 2.8 g of carbazole, 3.1 g of[3-(triphenylsilyl)phenyl]boronic acid, 0.16 g oftetrakis(triphenylphophine) palladium, 8.2 g of sodium tert butoxide,and 480 mg of 2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl weredissolved in 170 ml of xylene and distilled for two days under N₂atmosphere. The reaction compound was dried with magnesium sulfate, andthe residue obtained by evaporating a solvent was separated and purifiedby silica gel column chromatography to obtain 1.9 g (78% yield) ofCompound 13. Compound 13 was identified by LC-MS and ¹H -NMR.

Synthesis Example 3: Synthesis of Compound 20

Synthesis of Intermediate 20-1

After 5.9 g of (3-Methoxypyridin-2-yl) boronic acid, 9.8 g of6-chloro-2-iodopyridin-3-amine, 16 g of potassium carbonate, 250 mL oftoluene, 13 mL of distilled water, and 1.3 g ofTetrakis(triphenylphosphine)palladium(0) were mixed and reacted, 5 ml ofTHF, 10 ml of glacial acetic acid, and 11.3 g of tert-butyl nitrite weresubsequently added thereto for further reaction. The obtained compoundwas diluted with water, and then separated and purified by silica gelcolumn chromatography to obtain 3.2 g of Intermediate 20-1.

Synthesis of Compound 20

3.2 g of Intermediate 20-1, 2.8 g of carbazole, 3.1 g of[3-(triphenylsilyl)phenyl]boronic acid, 0.16 g oftetrakis(triphenylphophine) palladium, 8.2 g of sodium tert butoxide,and 480 mg of 2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl weredissolved in 170 ml of xylene and distilled for two days under N₂atmosphere. The reaction compound was dried with magnesium sulfate, andthe residue obtained by evaporating a solvent was separated and purifiedby silica gel column chromatography to obtain 1.9 g (yield of 78%) ofCompound 20. Compound 20 was identified by LC-MS and ¹H -NMR.

Synthesis Example 4: Synthesis of Compound 32

Synthesis of Compound 32

3.2 g of Intermediate 13-1, 2.8 g of 9H-3,9′-bicarbazole, 3.1 g ofTriphenylsilyl chloride, 0.16 g of tetrakis(triphenylphophine)palladium, 8.2 g of sodium tert butoxide, and 480 mg of2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl were dissolved in 170ml of xylene and distilled for two days under N₂ atmosphere. Thereaction compound was dried with magnesium sulfate, and the residueobtained by evaporating a solvent was separated and purified by silicagel column chromatography to obtain 1.7 g (yield of 76%) of Compound 32.Compound 32 was identified by LC-MS and ¹H -NMR.

Synthesis Example 5: Synthesis of Compound 33

Synthesis of Compound 33

3.2 g of Intermediate 13-1, 2.8 g of 9H-3,9′-bicarbazole, 3.1 g of[4-(triphenylsilyl)phenyl]boronic acid, 0.16 g oftetrakis(triphenylphophine) palladium, 8.2 g of sodium tert butoxide,and 480 mg of 2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl weredissolved in 170 ml of xylene and distilled for two days under N₂atmosphere. The reaction compound was dried with magnesium sulfate, andthe residue obtained by evaporating a solvent was separated and purifiedby silica gel column chromatography to obtain 1.7 g (yield of 76%) ofCompound 33. Compound 33 was identified by LC-MS and ¹H -NMR.

Synthesis Example 6: Synthesis of Compound 34

Synthesis of Intermediate 34-1

200 ml of AcOH was mixed with a compound obtained by distilling amixture including 4.9 g of 5-chloro-3-iodopyridin-2-amine, 3.4 g of4-bromothiophenol, 0.2 g of CuI, 2.4 g of ethylene glycol, 5.2 g ofpotassium carbonate, and 100 ml of isopropanol under N₂ atmosphere for24 hours, and then 1.64 g of Bu^(t)ONO was added dropwise thereto forthe reaction. The obtained compound was separated and purified by silicagel column chromatography to obtain 3.2 g of Intermediate 34-1(6-bromo-3-chlorobenzo[4, 5]thieno[2, 3-b]pyridine).

Synthesis of Compound 34

3.2 g of Intermediate 34-1, 2.8 g of 9H-3,9′-bicarbazole, 3.1 g ofTriphenylsilyl chloride, 0.16 g of tetrakis(triphenylphophine)palladium, 8.2 g of sodium tert butoxide, and 480 mg of2-dichlorohexyl-phosphino-2′,6′-dimethoxybiphenyl were dissolved in 170ml of xylene and distilled for two days under N₂ atmosphere. Thereaction compound was dried with magnesium sulfate, and the residueobtained by evaporating a solvent was separated and purified by silicagel column chromatography to obtain 1.7 g (yield of 76%) of Compound 34.Compound 34 was identified by LC-MS and ¹H -NMR.

TABLE 1 MS/FAB Compound ¹H NMR (CDCl₃, 400 MHz) found  9 9.24(1H, S),8.73(1H, S), 8.55 (1H, D), 8.19(1H, D), 669.22 8.09(1H, S),7.88-7.94(2H, m), 7.35-7.64(22H, m), 7.16-7.20(2H, m) 13 8.71(1H, S),8.55(1H, S), 9.19(1H, S), 7.46- 668.23 7.94(6H, m), 7.35-7.64(21H, m),7.16-7.20(2H, m) 20 8.55(1H, D), 8.43(1H, D), 7.88-8.02(6H, m), 669.227.77(1H, D), 7.46-7.64(3H, m), 7.33-7.46(17H, m), 7.16-7.21(2H, m) 328.87(1H, S), 8.55(2H, D), 8.19(1H, D), 8.03(1H, S), 757.25 7.94(2H, D),7.67-7.74(3H, m), 7.31-7.50(20H, m), 7.16-7.20(3H, m) 33 9.24(1H, S),8.55(2H, S), 8.19(1H, S), 8.09(1H, S), 833.29 7.88-7.94(3H, m),7.31-7.74(28H, m), 7.16- 7.20(3H, m) 34 8.87(1H, S), 8.55(2H, D),8.19(1H, D), 8.10(1H, D), 773.23 8.03(1H, S), 7.90-7.94(3H, m),7.67-7.72(2H, m), 7.58(1H, D), 7.35-7.50(20H, m), 7.16-7.20(3H, m)

Evaluation Example Example 1

As an anode, a glass substrate with 15 Ωcm² (1,200 Å) ITO thereon, whichwas manufactured by Corning Inc., was cut to a size of 50 mm×50 mm×0.7mm, and the glass substrate was sonicated by utilizing isopropyl alcoholand pure water for 5 minutes each, and then irradiated with ultraviolet(UV) light for 30 minutes and exposed to ozone for cleaning. Then, theresultant glass substrate was loaded onto a vacuum deposition apparatus.Compound HT1 and F4-TCNQ were co-deposited at a weight ratio of 98:2 onthe substrate to form a first hole transport layer having a thickness of100 Å, and compound HT1 was deposited on the first hole transport layerto form a second hole transport layer having a thickness of 700 Å. TCTAwas vacuum deposited on the second hole transport layer to form anelectron blocking layer having a thickness of 100 Å.

Compound 13 and BD1 (dopant) were co-deposited on the electron blockinglayer such that the concentration of the dopant was 10 wt %, therebyforming an emission layer having a thickness of 350 Å. Subsequently,after DIC-TRZ was deposited on the emission layer to form a holeblocking layer having a thickness of 100 Å, ET1 and LiQ wereco-deposited as an electron transport compound on the hole blockinglayer at a ratio of 5:5 to form an electron transport layer having athickness of 300 Å. LiF as a halogenated alkali metal was deposited onthe electron transport layer to form an electron injection layer havinga thickness of 10 Å, and Al (cathode) was vacuum deposited thereon to athickness of 1000 Å, thereby forming an LiF/Al electrode, resulting incompleting the manufacture of an organic light-emitting device.

Example 2

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 33 was utilized instead of Compound 13to form the emission layer.

Example 3

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 33 and DIC-TRZ were utilized at a weightratio of 5:5 instead of Compound 13 to form the emission layer.

Example 4

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 33 and DIC-TRZ were utilized at a weightratio of 5:5 instead of Compound 13, and compound BD1 (10 wt %) andcompound FD23 (1 wt %) were utilized as a dopant, to form the emissionlayer.

Example 5

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 33 and DIC-TRZ were utilized at a weightratio of 7:3 instead of Compound 13 to form the emission layer.

Example 6

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 33 and DIC-TRZ were utilized at a weightratio of 7:3 instead of Compound 13, and compound BD1 (10 wt %) andcompound FD23 (1 wt %) were utilized as a dopant, to form the emissionlayer.

Example 7

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 20 was utilized instead of Compound 13to form the emission layer.

Example 8

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 9 was utilized instead of Compound 13 toform the emission layer.

Example 9

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 32 was utilized instead of Compound 13to form the emission layer.

Example 10

An organic light-emitting device was prepared in the same manner as inExample 1, except that Compound 34 was utilized instead of Compound 13to form the emission layer.

Comparative Examples 1 to 5

An organic light-emitting device was prepared in the same manner as inExample 1, except that compounds described in table 2 were utilizedinstead of Compound 13 to form the emission layer.

With respect to the organic light-emitting devices prepared in Examples1 to 10 and Comparative Examples 1 to 5, driving voltage (V) andlifespan of T95 were measured in a current density of 10 mA/cm² and theresults are shown in table 2. When the initial brightness (@10 mA/cm²)is taken as 100%, T95 lifespan represents the time required for thebrightness to reach 95%.

TABLE 2 Emission layer Driving T95 lifespan host Dopant voltage (V) (%)Comparative CBP BD1 5.2 100% Example 1 Comparative Compound A BD1 4.8 95% Example 2 Comparative Compound B BD1 4.8 120% Example 3 ComparativeCompound C BD1 5.7  91% Example 4 Comparative Compound D BD1 5.4 131%Example 5 Example 1 Compound BD1 4.9 207% 13 Example 2 Compound BD1 4.8230% 33 Example 3 Compound BD1 4.3 246% 33:DIC—TRZ (5:5) Example 4Compound BD1: 4.5 221% 33:DIC—TRZ FD23 (5:5) Example 5 Compound BD1 4.1255% 33:DIC—TRZ (7:3) Example 6 Compound BD1: 4.2 261% 33:DIC—TRZ FD23(7:3) Example 7 Compound BD1 5.0 211% 20 Example 8 Compound 9 BD1 4.8214% Example 9 Compound BD1 4.8 227% 32 Example 10 Compound BD1 4.6 217%34

From the results of table 2, the organic light-emitting devices ofExamples 1 to 10, each utilizing compounds according to an embodiment ofthe present disclosure as an emission layer host, have lower drivingvoltage compared to the organic light-emitting devices of ComparativeExamples 1 to 5, and have significantly improved lifespan.

The heterocyclic compound according to an embodiment of the presentdisclosure has a bipolar characteristic, and thus stability of acompound may be improved, and organic light-emitting device includingthe heterocyclic compound may have high efficiency and long lifespan.

The terminology used herein is for the purpose of describing particularexample embodiments only and is not intended to be limiting of theinvention. As used herein, the singular forms “a,” “an” and “the” areintended to include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises” and/or “comprising,” when used in this specification,specify the presence of stated features, integers, steps, operations,elements, and/or components, but do not preclude the presence oraddition of one or more other features, integers, steps, operations,elements, components, and/or groups thereof.

It will be understood that when an element or layer is referred to asbeing “on”, “connected to”, “coupled to”, or “adjacent to” anotherelement or layer, it can be directly on, connected to, coupled to, oradjacent to the other element or layer, or one or more interveningelements or layers may be present. In contrast, when an element or layeris referred to as being “directly on,” “directly connected to”,“directly coupled to”, or “immediately adjacent to” another element orlayer, there are no intervening elements or layers present. As usedherein, the term “substantially,” “about,” and similar terms are used asterms of approximation and not as terms of degree, and are intended toaccount for the inherent deviations in measured or calculated valuesthat would be recognized by those of ordinary skill in the art.Moreover, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein. All suchranges are intended to be inherently described in this specificationsuch that amending to expressly recite any such subranges would complywith the requirements of 35 U.S.C. § 112, first paragraph, or 35 U.S.C.§ 112(a), and 35 U.S.C. § 132(a).

Expressions such as “at least one of,” when preceding a list ofelements, modify the entire list of elements and do not modify theindividual elements of the list. Further, the use of “may” whendescribing embodiments of the inventive concept refers to “one or moreembodiments of the inventive concept.” Also, the term “exemplary” isintended to refer to an example or illustration.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments. While one or more embodiments have beendescribed with reference to the figures, it will be understood by thoseof ordinary skill in the art that various changes in form and detailsmay be made therein without departing from the spirit and scope asdefined by the following claims, and equivalents thereof.

What is claimed is:
 1. An organic light-emitting device comprising: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode, theorganic layer comprising an emission layer; wherein the organiclight-emitting device comprises one or more heterocyclic compoundsrepresented by Formula 1:

wherein, in Formulae 1 to 3, Y₁ is O or S, Cz is a group represented byFormula 2, n1 and n2 are each independently an integer from 0 to 4, anda sum of n1 and n2 is 1 or more, A₁₁, A₁₂, A₂₁, and A₂₂ are eachindependently selected from a benzene ring, a pyridine ring, apyrimidine ring, and a pyridazine ring, and at least one of A₁₁ and A₁₂is selected from a pyridine ring, a pyrimidine ring, and a pyridazinering, L₁, L₂, and L₂₁ to L₂₃ are each independently selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,a1, a2, and a21 to a23 are each independently an integer from 0 to 3,R₁, R₂, R₂₁, and R₂₂ are each independently selected from a grouprepresented by Formula 3, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an am idino group, ahydrazine group, a hydrazone group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂), wherein atleast one of R₁, R₂, R₂₁, and R₂₂ is a group represented by Formula 3,R₃, R₄, R₂₃, and R₂₄ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂), b1, b2, b21, and b22are each independently an integer from 1 to 5, c1, c2, c21, and c22 areeach independently an integer from 1 to 4, c3, c4, c23, and c24 are eachindependently an integer from 0 to 4, Ar₃₁ to Ar₃₃ are eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), wherein Q₁ to Q₃, Q₁₁to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * indicates a binding site to aneighboring atom.
 2. The organic light-emitting device of claim 1,wherein the emission layer comprises the one or more heterocycliccompounds.
 3. The organic light-emitting device of claim 2, wherein: theone or more heterocyclic compounds comprised in the emission layer serveas a host, and the emission layer further comprises at least oneselected from a phosphorescent dopant and a fluorescent dopant.
 4. Theorganic light-emitting device of claim 2, wherein: the one or moreheterocyclic compounds comprised in the emission layer serve as a host,and the emission layer further comprises at least one of an electrontransport host and a hole transport host.
 5. The organic light-emittingdevice of claim 2, wherein: the one or more heterocyclic compoundscomprised in the emission layer serve as a host, and the emission layerfurther comprises an electron transport host comprising at least one 7electron-depleted nitrogen-containing ring.
 6. The organiclight-emitting device of claim 2, wherein: the organic layer furthercomprises at least one layer selected from an electron blocking layerbetween the first electrode and the emission layer and a hole blockinglayer between the emission layer and the second electrode, the electronblocking layer comprises the one or more heterocyclic compoundsrepresented by Formula 1 when the organic layer comprises the electronblocking layer, and the hole blocking layer comprises the one or moreheterocyclic compounds represented by Formula 1 when the organic layercomprises the hole blocking layer.
 7. The organic light-emitting deviceof claim 1, wherein: the first electrode is an anode, the secondelectrode is a cathode, the organic layer comprises the one or moreheterocyclic compounds represented by Formula 1, the organic layercomprises a hole transport region between the first electrode and theemission layer and an electron transport region between the emissionlayer and the second electrode, the hole transport region comprises ahole injection layer, a hole transport layer, an emission auxiliarylayer, and/or an electron blocking layer, and the electron transportregion comprises a buffer layer, a hole blocking layer, an electrontransport layer, and/or an electron injection layer.
 8. The organiclight-emitting device of claim 7, wherein the hole transport regioncomprises a p-dopant having a lowest unoccupied molecular orbital (LUMO)energy level of less than −3.5 eV.
 9. A heterocyclic compoundrepresented by Formula 1:

wherein, in Formulae 1 to 3, Y₁ is O or S, Cz is a group represented byFormula 2, n1 and n2 are each independently an integer from 0 to 4, anda sum of n1 and n2 is 1 or more, A₁₁, A₁₂, A₂₁, and A₂₂are eachindependently selected from a benzene ring, a pyridine ring, apyrimidine ring, and a pyridazine ring, and at least one of A₁₁ and A₁₂is selected from a pyridine ring, a pyrimidine ring, and a pyridazinering, L₁, L₂, and L₂₁ to L₂₃ are each independently selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkylene group, a substitutedor unsubstituted C₁-C₁₀ heterocycloalkylene group, a substituted orunsubstituted C₃-C₁₀ cycloalkenylene group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenylene group, a substituted orunsubstituted C₆-C₆₀ arylene group, a substituted or unsubstitutedC₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalentnon-aromatic condensed polycyclic group, and a substituted orunsubstituted divalent non-aromatic condensed heteropolycyclic group,a1, a2, and a21 to a23 are each independently an integer from 0 to 3,R₁, R₂, R₂₁, and R₂₂ are each independently selected from a grouprepresented by Formula 3, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a substituted or unsubstitutedC₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group,a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted orunsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂),—B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂), wherein atleast one of R₁, R₂, R₂₁, and R₂₂ is a group represented by Formula 3,R₃, R₄, R₂₃, and R₂₄ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁)(Q₂), and —P(═O)(Q₁)(Q₂), b1, b2, b21, and b22are each independently an integer from 1 to 5, c1, c2, c21, and c22 areeach independently an integer from 1 to 4, c3, c4, c23, and c24 are eachindependently an integer from 0 to 4, Ar₃₁ to Ar₃₃ are eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), wherein Q₁to Q₃, Q₁₁ toQ₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amino group, an amidino group, a hydrazine group, ahydrazone group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * indicates a binding site to aneighboring atom.
 10. The heterocyclic compound of claim 9, wherein: A₁₁is a benzene ring and A₁₂ is a pyridine ring, A₁₁ is a pyridine ring andA₁₂ is a benzene ring, or each of A₁₁ and A₁₂ is a pyridine ring. 11.The heterocyclic compound of claim 9, wherein: i) n1 is 1, n2 is 0, andR₂ is a group represented by Formula 3; or ii) n1 is 1, n2 is 0, and R₂₁or R₂₂ is a group represented by Formula
 3. 12. The heterocycliccompound of claim 9, wherein the heterocyclic compound is represented byFormula 1A:

wherein, in Formula 1A, X₁ is C or N, X₂ is C or N, X₄ is C or N, X₅ isC or N, X₆ is C or N, X₇ is C or N, and X₈ is C or N, at least one ofX₁, X₂, and X₄ to X₈ is N, c1 is an integer from 1 to 3, c2 is aninteger from 1 to 4, c3 is an integer from 0 to 2, c4 is an integer from0 to 3, Y₁, Cz, L₁, L₂, a1, a2, R₁ to R₄, and b1 to b2 are each the sameas respectively defined in connection with Formula
 1. 13. Theheterocyclic compound of claim 9, wherein the heterocyclic compound isrepresented by one of Formulae 1A-1 to 1A-8:

wherein, in Formulae 1A-1 to 1A-8, X₁ is C or N, X₂ is C or N, X₄ is Cor N, X₅ is C or N, X₆ is C or N, X₇ is C or N, and X₈ is C or N, atleast one of X₁, X₂, and X₄ to X₈ is N, in Formulae 1A-1 to 1A-4, R₂₁ isa group represented by Formula 3, c3 is an integer from 0 to 3, c4 is aninteger from 0 to 4, c23 is an integer from 0 to 3, and c24 is aninteger from 0 to 4, in Formulae 1A-5 to 1A-8, R₂ is a group representedby Formula 3, c3 and c4 are each independently an integer from 0 to 3,and c23 and c24 are each independently an integer from 0 to 4, and Y₁,L₂, L₂₁, a2, a21, R₃, R₄, R₂₃, and R₂₄ are each the same as respectivelydefined in connection with Formulae 1 and
 2. 14. The heterocycliccompound of claim 13, wherein: one of X₁, X₂, and X₄ to X₈ is N, andremaining ones of X₁, X₂, and X₄ to X₈ are each C; X₁ and X₈ are each N,and X₂ and X₄ to X₇ are each C; X₂ and X₅ are each N, and X₁, X₄, and X₆to X₈ are each C; X₂ and X₈ are each N, and X₁ and X₄ to X₇ are each C;X₄ and X₅ are each N, and X₁, X₂, and X₆ to X₈ are each C; X₄ and X₇ areeach N, and X₁, X₂, X₅, X₆, and X₈ are each C; or X₄ and X₈ are each N,and X₁, X₂, and X₅ to X₇ are each C.
 15. The heterocyclic compound ofclaim 9, wherein L₁, L₂, and L₂₁ to L₂₃ are each independently selectedfrom: a cyclobutylene group, a cyclopentylene group, a cyclohexylenegroup, a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a spiro-fluorene-benzofluorenylene group, abenzofluorenylene group, a dibenzofluorenylene group, a phenalenylenegroup, a phenanthrenylene group, an anthracenylene group, afluoranthenylene group, a triphenylenylene group, a pyrenylene group, achrysenylene group, a naphthacenylene group, a picenylene group, aperylenylene group, a pyridinylene group, a pyrazinylene group, apyrimidinylene group, a quinolinylene group, an isoquinolinylene group,a benzoquinolinylene group, a naphthyridinylene group, a quinoxalinylenegroup, a quinazolinylene group, a thiophenylene group, a furanylenegroup, a carbazolylene group, an indolylene group, an isoindolylenegroup, a benzofuranylene group, a benzothiophenylene group, adibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, and adibenzosilolylene group; and a cyclobutylene group, a cyclopentylenegroup, a cyclohexylene group, a phenylene group, a pentalenylene group,an indenylene group, a naphthylene group, an azulenylene group, aheptalenylene group, an indacenylene group, an acenaphthylene group, afluorenylene group, a spiro-bifluorenylene group, aspiro-fluorene-benzofluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apyridinylene group, a pyrazinylene group, a pyrimidinylene group, aquinolinylene group, an isoquinolinylene group, a benzoquinolinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a thiophenylene group, a furanylene group, acarbazolylene group, an indolylene group, an isoindolylene group, abenzofuranylene group, a benzothiophenylene group, a dibenzofuranylenegroup, a dibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, and a dibenzosilolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an am idino group, ahydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, abiphenyl group, a terphenyl group, a pentalenyl group, an indenyl group,a naphthyl group, an azulenyl group, a heptalenyl group, an indacenylgroup, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a naphthyridinyl group, a quinoxalinyl group, a quinazolinylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂).
 16. The heterocyclic compound of claim 9, wherein L₁, L₂,and L₂₁ to L₂₃ are each independently selected from groups representedby Formulae 3-1 to 3-38:

wherein, in Formulae 3-1 to 3-38, Y₁ is O, S, C(Z₃)(Z₄), N(Z₅), orSi(Z₆)(Z₇), Z₁ to Z₇ are each independently selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenylgroup, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinylgroup, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), d2 is 1 or 2, d3 is an integer from 1 to 3, d4 is aninteger from 1 to 4, d5 is an integer from 1 to 5, d6 is an integer from1 to 6, d8 is an integer from 1 to 8, Q₃₁ to Q₃₃ are each independentlyselected from hydrogen, deuterium, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxygroup, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalentnon-aromatic condensed polycyclic group, a monovalent non-aromaticcondensed heteropolycyclic group, a biphenyl group, and a terphenylgroup, and * and *′ each indicate a binding site to a neighboring atom.17. The heterocyclic compound of claim 9, wherein a1, a2, and a21 to a23are each independently 0 or
 1. 18. The heterocyclic compound of claim 9,wherein Aral to Ar33 are each independently selected from groupsrepresented by Formulae 5-1 to 5-81:

wherein, in Formulae 5-1 to 5-81, Y₃₁ is selected from O, S, N(Z₃₃),C(Z₃₄)(Z₃₅), and Si(Z₃₆)(Z₃₇), Z₃₁ to Z₃₇ are each independentlyselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazine group, ahydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyridinyl group, a pyrazinyl group, a pyrimidinyl group, a quinolinylgroup, an isoquinolinyl group, a benzoquinolinyl group, a naphthyridinylgroup, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a triazinyl group, a dibenzofuranyl group, adibenzothiophenyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and—B(Q₃₁)(Q₃₂), e2 is 1 or 2, e3 is an integer from 1 to 3, e4 is aninteger from 1 to 4, e5 is an integer from 1 to 5, e6 is an integer from1 to 6, e7 is an integer from 1 to 7, e9 is an integer from 1 to 9, Q₃₁to Q₃₃ are each independently selected from hydrogen, deuterium, aC₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryl group, a C₁-C₂₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, and * indicates a binding site to aneighboring atom.
 19. The heterocyclic compound of claim 9, wherein R₁,R₂, R₂₁, and R₂₂are each independently selected from: a grouprepresented by Formula 3, hydrogen, deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, a C₁-C₂₀ alkyl group, anda C₁-C₂₀ alkoxy group; a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group,each substituted with at least one selected from deuterium, —F, —Cl,—Br, —I, a cyano group, a phenyl group, and a biphenyl group; acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group; and a cyclopentyl group, acyclohexyl group, a cycloheptyl group, a cyclopentenyl group, acyclohexenyl group, a phenyl group, a naphthyl group, a fluorenyl group,a spiro-bifluorenyl group, a spiro-fluorene-benzofluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a pyrenyl group, aphenalenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrrolyl group, athiophenyl group, a furanyl group, a silolyl group, an imidazolyl group,a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, apyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolylgroup, an indazolyl group, a purinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, anaphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, acinnolinyl group, a phenanthridinyl group, an acridinyl group, aphenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, abenzofuranyl group, a benzothiophenyl group, a benzosilolyl group, anisobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group,a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinylgroup, a dibenzofuranyl group, a dibenzothiophenyl group, adibenzosilolyl group, a carbazolyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinylgroup, an imidazopyrimidinyl group, an oxazolopyridinyl group, athiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenylgroup, an azaspiro-bifluorenyl group, an azacarbazolyl group, anazadibenzofuranyl group, an azadibenzothiophenyl group, anazadibenzosilolyl group, a biphenyl group, and a terphenyl group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazine group, a hydrazone group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptylgroup, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, aspiro-fluorene-benzofluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a pyrenyl group, a phenalenyl group, aphenanthrenyl group, an anthracenyl group, a fluoranthenyl group, atriphenylenyl group, a pyrrolyl group, a thiophenyl group, a furanylgroup, a silolyl group, an imidazolyl group, a pyrazolyl group, athiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolylgroup, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, apyridazinyl group, an indolyl group, an isoindolyl group, an indazolylgroup, a purinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, a benzofuranyl group, abenzothiophenyl group, a benzosilolyl group, an isobenzothiazolyl group,a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an oxadiazolyl group, a triazinyl group, adibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group,a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group,a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an oxazolopyridinyl group, a thiazolopyridinyl group, abenzonaphthyridinyl group, an azafluorenyl group, anazaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranylgroup, an azadibenzothiophenyl group, an azadibenzosilolyl group, abiphenyl group, and a terphenyl group.
 20. The heterocyclic compound ofclaim 9, wherein the heterocyclic compound is selected from Compounds 1to 35: